Ethanol → HCID 14104007, compound

HRID 650660Notes

Reaction equation

HRID 650660 reaction equation
[CH:1]1([CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.[CH2:17](O)[CH3:18]>>[CH:1]1([CH2:7][C@@H:8]([C:10]([O:12][CH2:17][CH3:18])=[O:11])[NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 7124213-Cyclohexyl-L-alanine

Product 1

HCID 14104007HCID 14104007, compound

Conditions

Temperature
0 °C

Procedure

b-cyclohexyl alanine (1.5 g) is dissolved in absolute ethanol (75 ml) and the solution cooled to 0° C. Thionyl chloride (1.1 ml) is added dropwise over a period of 10-15 minutes, the solution allowed to warn to room temperature, and then stirred at room temperature for about 18 hours. The reaction mixture is evaporated in vacuo, toluene is azeotroped twice from the residue, and the residue is taken up into ethyl acetate. The ethyl acetate solution is washed with water, 1 N sodium hydroxide, water, brine, dried over sodium sulfate, filtered, and evaporated in vacuo to give b-cyclohexyl alanine, ethyl ester.

Workup

  1. customto warn to room temperature
  2. customThe reaction mixture is evaporated in vacuo, toluene
  3. customis azeotroped twice from the residue
  4. washThe ethyl acetate solution is washed with water, 1 N sodium hydroxide, water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-854e1459eef54de38cfc718e743549c1
Source dataset
uspto-grants-2001_08
Patent number
US06274705B1

Reaction notes

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